Protective Effects of Dihydromyricetin against •OH-Induced Mesenchymal Stem Cells Damage and Mechanistic Chemistry

Protective Effects of Dihydromyricetin against •OH-Induced Mesenchymal Stem Cells Damage and Mechanistic Chemistry
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二氢杨梅素对 OH 诱导的间充质干细胞损伤的保护作用及机制化学

DOI:
10.3390/molecules21050604
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发表时间:
2016-05-01
期刊:
影响因子:
4.6
通讯作者:
Chen, Dongfeng
Chen, Dongfeng
中科院分区:
化学2区
文献类型:
--
作者:
Li, Xican;Liu, Jingjing;Chen, Dongfeng

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作为 Ampelopsisgrosedentata 中的天然类黄酮,使用 MTT [3-(4,5-二甲基噻唑-2-基)-2,5-二苯基] 测定和流式细胞仪观察到二氢杨梅素(DHM,2R,3R-3,5,7,3',4',5'-六羟基-2,3-二氢黄酮醇)可增加中心点 OH 处理的间充质干细胞的活力细胞计数分析。这种保护作用表明 DHM 可能是细胞移植治疗的有益药物。机理化学研究表明,与杨梅素相比,DHM对ABTS(+)中心点(2,2'-azino-bis(3-乙基苯并噻唑啉-6-磺酸基)的清除和还原Cu2+的效果较差,但具有较高的中心点O-2(-)和DPPH中心点(1,1-二苯基-2-三硝基苯肼自由基)的清除活性。 Fe2+ 在 589 nm 处具有最大吸收,因此,DHM 的这种保护作用可能是通过直接自由基清除和 Fe2+ 螯合产生的,推测 2,3-双键的氢化可通过阻止更大的 pi-pi 共轭系统的形成来减少 ET 过程。杨梅苷被认为在中心点 O-2(-) 和 DPPH 中心点自由基清除过程中阻碍原子转移,在 DHM 中,Fe2+ 螯合效应实际上可归因于 5,3',4',5'-OH 和 4-C=O 基团,而 3-OH 基团本身既不能清除自由基,也不能螯合金属。
As a natural flavonoid in Ampelopsis grossedentata, dihydromyricetin (DHM, 2R,3R-3,5,7,3',4',5'-hexahydroxy-2,3-dihydroflavonol) was observed to increase the viability of center dot OH-treated mesenchymal stem cells using a MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl] assay and flow cytometry analysis. This protective effect indicates DHM may be a beneficial agent for cell transplantation therapy. Mechanistic chemistry studies indicated that compared with myricetin, DHM was less effective at ABTS(+)center dot(2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonicacid radical) scavenging and reducing Cu2+, and had higher center dot O-2(-) and DPPH center dot (1,1-diphenyl-2-picrylhydrazyl radical) scavenging activities. Additionally, DHM could also chelate Fe2+ to give an absorption maximum at 589 nm. Hence, such protective effect of DHM may arise from its antioxidant activities which are thought to occur via direct radical-scavenging and Fe2+-chelation. Direct radical-scavenging involves an electron transfer (ET) pathway. The hydrogenation of the 2,3-double bond is hypothesized to reduce the ET process by blocking the formation of a larger pi-pi conjugative system. The glycosidation of the 3-OH in myricitrin is assumed to sterically hinder atom transfer in the center dot O-2(-) and DPPH center dot radical-scavenging processes. In DHM, the Fe2+-chelating effect can actually be attributed to the 5,3',4',5'-OH and 4-C=O groups, and the 3-OH group itself can neither scavenge radicals nor chelate metal.